Hydrazine → 4-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzoic Acid Hydrazide

HRID 253207Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[S:16][C:17]=2[CH3:18])=[CH:6][CH:5]=1.[NH2:30][NH2:31]>CO.O>[CH3:18][C:17]1[S:16][C:15]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[N:14][C:13]=1[CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH:30][NH2:31])=[O:2])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylethoxy]-benzoic acid methyl ester (Example 4, 410 mg, 1 mmol) in methanol (3 mL) add anhydrous hydrazine (0.32 ml, 10 mmol). Warm the resulting mixture to 60° C. and stir at this temperature for 66 hrs. Cool the resulting solution to room temperature, and add 3 drops of water. Filter the precipitate wash with ether to give the title compound (279 mg).

Workup

temperatureCool the resulting solution to room temperature
filtrationFilter the precipitate
washwash with ether

Sources & evidence

ORD record: ord-57d860cee51947d3b8bf0406d5835c8a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872032B2

Reaction notes

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